Home Cart Sign in  
Chemical Structure| 147460-41-1 Chemical Structure| 147460-41-1

Structure of 147460-41-1

Chemical Structure| 147460-41-1

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 147460-41-1 ]

CAS No. :147460-41-1
Formula : C6H4BrFO
M.W : 191.00
SMILES Code : OC1=CC(F)=CC=C1Br
MDL No. :MFCD00040939
InChI Key :HUVAOAVBKOVPBZ-UHFFFAOYSA-N
Pubchem ID :2724600

Safety of [ 147460-41-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H227-H315-H319-H335
Precautionary Statements:P305+P351+P338

Computational Chemistry of [ 147460-41-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 1.0
Molar Refractivity 36.12
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

20.23 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.87
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.63
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

2.71
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

2.67
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

2.48
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.47

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.17
Solubility 0.128 mg/ml ; 0.000669 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-2.71
Solubility 0.377 mg/ml ; 0.00197 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-2.96
Solubility 0.211 mg/ml ; 0.00111 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

Yes
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.6 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

2.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

0.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

1.24

Application In Synthesis of [ 147460-41-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 147460-41-1 ]

[ 147460-41-1 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 50-00-0 ]
  • [ 13659-23-9 ]
  • [ 147460-41-1 ]
  • [ 1009094-06-7 ]
YieldReaction ConditionsOperation in experiment
47% To a solution of MgCl2 (powder 325 mesh, 0.734 g, 7.71 mmol, 2 eq), paraformaldehyde (0.347 g, 11.57 mmol, 3 eq) and Et3N (1.08 mL, 7.71 mmol, 2 eq) in THF (20 mL) was added 276 (0.800 g, 3.68 mmol, 1 eq), heated in the microwave at 160 C for 15 min. TLC (3:2 Hexane:DCM) showed complete consumption of 3. THF was evaporated and the reaction mixture was taken up in EtOAc, washed with brine, dried, filtered and concentrated in vacuo to afford 0.52 g of 277 which was used without purification. Yield 47%
  • 2
  • [ 1895-39-2 ]
  • [ 147460-41-1 ]
  • [ 954235-83-7 ]
YieldReaction ConditionsOperation in experiment
58% With caesium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 15.0h; itermediteExthp1eI5. ?sulfOnamide ?,?a) .To a solutiOn of 2-brotho-5-fludrophenol (3g. 15.7 mmol) in DMF (5 ml) was added cesium carbonate (7.7 g, 23.56 mmol, 1.5 eq) and sodium chlorodifluoroacetate(6 g, 39.26 nimol;2:5 eq) and the reaction mixture was heated at 100C for 15 h. Thereaction mixture was then exttacted with Water and ethyl acetate (3 x 50 mI) Thecombined Organic layer was washed with water, brine and dried over sodium sulphate. The solvent was distilled off to afford the crude residue which was purified by column chromatography (60-120 silica ge110% ethyl acetate in hexane) in 58 % yield (2.2 g).
With caesium carbonate; In water; N,N-dimethyl-formamide; at 100.0℃; for 15.0h; Preparation Example 3 A mixture of 2-bromo-5-fluorophenol (3 g), sodium chlorodifluoroacetate (6 g), cesium carbonate (7.7 g), water (3 mL) and DMF (30 mL) was stirred under heating at an oil temperature of 100C for 15 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was washed with 1M aqueous sodium hydroxide solution, further washed with water, dried and concentrated under reduced pressure to obtain 1-bromo-2-(difluoromethoxy)-4-fluorobenzene (2.77 g).
With water; caesium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 2.0h; Intermediate Example Int 17.11 -Bromo-2-(dif luoromethoxy)-4-f luorobenzeneTo a stirred solution of 2-bromo-5-fluorophenol (21 .0 g) in DMF (600 mL) was added cesium carbonate (107.5 g), sodium chlorodifluoroacetate (52.3 g) and water (29.4 mL). The mixture was stirred at 100 C for 2 h. The mixture was filtrated and the resulting solution was extracted with pentane (4 x 400 mL). The combined organic layers were washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum, to give 7.14 g of the title compound as a crude product. Silica gel chromatography afforded 3.2 g of the title compound.1H-NMR (400MHz, DMSO-d6): delta [ppm] = 7.10 - 7.16 (m, 1 H), 7.34 (t, 1 H), 7.33 - 7.36 (m, 1 H), 7.79 (dd, 1 H).
  • 3
  • [ 147460-41-1 ]
  • [ 76-04-0 ]
  • [ 954235-83-7 ]
YieldReaction ConditionsOperation in experiment
With sodium carbonate; In N,N-dimethyl-formamide; at 90.0℃; Compound 15 (80 g, 0.42 mol) was dissolved in DMF (800 mL), and sodium carbonate (266 g, 2.5 mol) wasadded. The temperature was increased to 90 C. Chlorodifluoroacetic acid (191 g, 1.46 mol) was added dropwise. Afterthe completion of addition, temperature was maintained at 90 C to react overnight. The reaction solution is cooled toroom temperature, poured slowly into ice water, and extracted twice with ethyl acetate. The organic phases were combined,washed once with saturated brine, dried over anhydrous sodium sulfate, and spin-dried to obtain 95 g of crudeproduct, which was used directly in the next reaction. 1H NMR (400 MHz, CDCl3): delta 7.62-7.58 (m, 1H), 7.04-7.01 (m,1H), 6.93-6.88 (m, 1H), 6.57 (t, J = 72.8 Hz, 1H); MS (ESI) (m/z): [M+H]+ 240.9.
 

Historical Records

Technical Information

Categories

Related Functional Groups of
[ 147460-41-1 ]

Fluorinated Building Blocks

Chemical Structure| 496-69-5

A135776 [496-69-5]

2-Bromo-4-fluorophenol

Similarity: 0.95

Chemical Structure| 433939-27-6

A400666 [433939-27-6]

3-Bromo-5-fluorophenol

Similarity: 0.93

Chemical Structure| 450-88-4

A206906 [450-88-4]

1-Bromo-4-fluoro-2-methoxybenzene

Similarity: 0.91

Chemical Structure| 121219-03-2

A159557 [121219-03-2]

4-Bromo-3-fluorophenol

Similarity: 0.91

Chemical Structure| 2040-89-3

A115265 [2040-89-3]

2-Bromo-6-fluorophenol

Similarity: 0.89

Aryls

Chemical Structure| 496-69-5

A135776 [496-69-5]

2-Bromo-4-fluorophenol

Similarity: 0.95

Chemical Structure| 433939-27-6

A400666 [433939-27-6]

3-Bromo-5-fluorophenol

Similarity: 0.93

Chemical Structure| 450-88-4

A206906 [450-88-4]

1-Bromo-4-fluoro-2-methoxybenzene

Similarity: 0.91

Chemical Structure| 121219-03-2

A159557 [121219-03-2]

4-Bromo-3-fluorophenol

Similarity: 0.91

Chemical Structure| 2040-89-3

A115265 [2040-89-3]

2-Bromo-6-fluorophenol

Similarity: 0.89

Bromides

Chemical Structure| 496-69-5

A135776 [496-69-5]

2-Bromo-4-fluorophenol

Similarity: 0.95

Chemical Structure| 433939-27-6

A400666 [433939-27-6]

3-Bromo-5-fluorophenol

Similarity: 0.93

Chemical Structure| 450-88-4

A206906 [450-88-4]

1-Bromo-4-fluoro-2-methoxybenzene

Similarity: 0.91

Chemical Structure| 121219-03-2

A159557 [121219-03-2]

4-Bromo-3-fluorophenol

Similarity: 0.91

Chemical Structure| 2040-89-3

A115265 [2040-89-3]

2-Bromo-6-fluorophenol

Similarity: 0.89